ASYMMETRIC HALOGENATION OF CHIRAL IMIDE ENOLATES. A GENERAL APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE α-AMINO ACIDS.

Article abstract of DOI:10.1016/S0040-4039(00)95305-X

The chiral N-acyl oxazolidones 2, as the derived dibutyl boron enolates, have been demonstrated to undergo diastereoselective bromination and subsequent azide displacement to give the α-azido carboximides 4a (5 cases).These adducts may be hydrolyzed under mild conditions to the enantiomerically pure α-azido carboxylic acids 5a.